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bostonboston kidsboston things to doboston things to do kids — 15 Oct 2025

October Boston Activities for the Fam

October Boston Activities for the Fam

October Boston Activities for the Fam

We can’t help but obsess over the perfection that is New England autumn. The leaves changing and falling, crisp cool air, and the coziest of sweaters to keep us warm. Fall activities are a favorite for all of us at Tiny Hanger, as we all love to embrace Boston in the fall.

This weekend in Cambridge and Boston, the world’s largest Regatta returns with the fun and exciting bustling of food trucks, freebies, and the perfect view of the Charles! Come check out The Head of the Charles with the family this weekend from Friday October 17th- Sunday October 19th. 

Pro Tip: Memorial Drive is closed so your littles can bike, run and play on the street with no fear of cars coming by!

Tiny Hanger is so excited to participate in Wellesley Linden Square’s Halloween event this weekend! Come trick-or-treating at nearby participating shops, sample food from Oath Pizza and Playa Bowls. Create some crafts and even explore an instrument petting zoo! Join us Saturday October 18th from 1pm-3pm to celebrate. 

Pro Tip: Your little ones will be able to touch and explore a real life firetruck! A can’t miss event for your truck obsessed minis. 

Honey Pot Hill Orchards is a favorite of mine. This place is postcard New England. Pick apples, explore a maze, take a hayride, and so much more! This is the perfect photo op to create those unforgettable memories. 

Pro Tip: Honey Pot Hill Orchards has an amazing petting zoo where your little one can even feed animals! 

A weekend in Salem in October is the perfect staple to the Boston lifestyle. There’s so much to explore even just walking around! So many cute stores, museums, and tours you won’t be bored. We love Curly Girl Candy Shop for a sweet treat. 

Pro Tip: Take the train to Salem! Avoid the traffic, parking, and headache with a fun train ride that your little ones will be wowed by!

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